Taking The Plunge

Taking The Plunge

Four years ago today, I was immersed in the American Choral Directors Association National Conference in Dallas. It was my first ACDA conference, and I had hit the ground running: I was catching up with colleagues, trying to make new contacts, and getting the lay of the land so that I could be better-prepared for the next time. At the same time, I was frantically finishing parts for an orchestral commission, suffering through horrible edits for a now-abandoned choral music recording project, and mentally preparing for a major life change: when I got back to New York, I was going to quit my day job and go full-time as a freelance composer.

At that point, I’d been working for a few years as the Accounts Payable guy for a historic non-profit theater in Midtown, and it had been wearing me down. I’d worked office jobs before—lots, in fact—and mostly, for some reason, in finance despite the fact that my degrees are all in music. I’d been a Fund of Hedge Funds administrator on Wall Street, I’d temped heavily for financial services firms, and had even assisted the Finance Department of the company that manages the Empire State Building.

I composed on evenings and weekends when I had the energy, and stole time away during the day job to handle some of my musical admin tasks and to “network” on Twitter. The 10-to-6 thing didn’t bother me overmuch, and the work itself was easy enough, but more often than not I came home from the job frustrated and angry and in no mood to be creative. The atmosphere at the job was, in short, toxic. That’s nothing new to most 9-to-5ers, and I’d had my share of bad jobs before, but it made the sacrifice of my time and energy chafe that much more.

And in retrospect, I was also in the midst of a delayed quarter-life crisis. I was 30, nearly 31, and surrounded by people who had walked away from their art long ago in favor of financial security, and were palpably miserable because of it. How long would it be until I was one of those souls who looked back wistfully at their happier days as an artist while filing another TPS report? I’d been in NYC for nearly 10 years at that point, and although I’d accomplished a fair amount, I hadn’t moved halfway across the country to one of the most expensive and difficult places to live so that I could play it safe. If all I’d wanted was security, I could have stayed in Normal, IL (yes, Normal), and gotten a job at State Farm.

So the day I got back from Dallas, I sat down with my boss and gave my notice.

Laptop with music notation software program on screen on table with glass of orange juice on the side

In the months leading up this, I’d spent a lot of time talking with my then-boyfriend/now-husband about the decision, and he was 100% on board. I had some money saved up, and I was confident that between the momentum I was gaining as a composer and all of my various side-hustles, I could replace enough of the W-2 income I’d be losing with new musical income and new side-hustle clients.

I had also been doing a lot of research. I read countless articles, blog posts, and books about living as a freelancer, and I was a devotee of a handful of podcasts by successful freelance writers. The common refrain was, it’s not easy, but with hard work and persistence, you can make this lifestyle work for you.

One of the best resources I’d come across, and one I still swear by today, was Kristine Kathryn Rusch’s Freelancer’s Survival Guide. In the book, Ms. Rusch tackles everything from adjusting your mindset about being your own boss, to handling your freelance finances, to the types of setbacks you can expect and how to overcome them, to negotiating and networking and assessing risk. Her insights into our motivations and behaviors when it comes to the idea of “work” are eye-opening, and for that alone I think that the book should be required reading for anyone who works any type of job, whether it’s freelance or not.

I also devoured David Cutler’s The Savvy Musician, Angela Myles Beeching’s Beyond Talent, and Jackie Battenfield’s The Artist’s Guide; scoured the blogs of writers Kristine Kathryn Rusch, Dean Wesley Smith, and Joe Konrath (titans of indie publishing who regularly write blog posts to help their fellow writers find their path); and hung on every word of The Creative Penn and the Self Publishing Podcast.

All of these resources will tell you that freelancing isn’t for everyone, for any number of reasons. Some people are just risk averse, and prefer having stability: for families that rely on two stable incomes, going freelance is often too risky a proposition. For some, the uncertainty can be psychologically unhealthy, since modern society so often links self-worth with “success”, especially financial success. And some people are, quite reasonably, content to earn their living separate from their art. We each have different values and needs, and we all have our reasons for wanting or not wanting to go freelance.

My good friend Ed Windels wrote some excellent posts here about being a composer with a day job. In preparing to write this first article, I re-read those, and agree 100% with what he has to say on the subject, and find there to be remarkable overlap in his views on what it takes to be a 5-to-9 artist and my own on what it takes to be a full-time freelancer. Both paths are difficult and take an exceptional amount of discipline and sacrifice. Neither is inherently better than the other: so long as it works for you, it’s the right path.

For me, I decided that I needed the change, and wanted to see if I could make it work.

Pages of sheet music from four different projects

So how was this whole thing supposed to work? I was on the precipice of giving up a very comfortable salary, staring into the complete unknown. Surely I had a plan?

At the point where I decoupled from the day job, I had two commissions lined up, and a handful of premieres on the horizon. It was a nice way to start my freelance life, but thanks to my work on Wall St., I was familiar with the caveat, “Past performance is not an indicator of future results.” I couldn’t rest on those laurels, and just wait for the next thing to come along. I also knew that I couldn’t immediately rely on meaningful income from music, so I would have to make up the shortfall from my now-former job in another way.

I’ve designed websites for musicians since 2007, and have done professional-level music copying work for about as long, so I could take on more work in those areas to stay financially afloat, and spend the remainder of my time on composing and growing my network of contacts. I was prepared to expand my web design business, and started canvassing local businesses in my neighborhood, looking for leads on potential new clients. A handful of new web clients could keep me afloat for months without taking up all of my time. I also let it be known to a few contacts that I was available for more engraving work, which paid well, and took a blessedly finite amount of time.

Musically, I was prepared to go deep into workhorse mode. I keep a spreadsheet of pieces that I want to write, so I wasn’t going to be at a loss for ideas; and, while I would certainly do my best to hunt down new commissions, I felt it just as important to keep writing regardless. If I was going to make it, I was going to have to keep expanding my catalog in meaningful ways.

Those of you who have followed my writing or my podcasts know that I take the firm stance that every piece you write, once it is finished, is a product in your catalog, a new asset on your books. Building on that, I made the decision that I would be better served building my catalog where I felt it needed growth even when the new works weren’t commissioned. More works—more assets—meant more opportunities.

So, armed with a plan and the collected knowledge and wisdom of the artists who I’d been following and studying, I set off as a full-time freelance composer.

Within months, everything had gone wrong.

Dennis Tobenski

Dennis Tobenski is a composer, vocalist, and advocate for new music and living composers. He hosts two music business-centered podcasts aimed at helping composers and performers to learn more about the practical aspects of their careers: the Music Publishing Podcast, a weekly, hour-long conversation with other professionals in the field of concert music, and The Composer’s Guide to Doing Business, where he answers questions and discusses current issues within the new music community.


NewMusicBox provides a space for those engaged with new music to communicate their experiences and ideas in their own words. Articles and commentary posted here reflect the viewpoints of their individual authors; their appearance on NewMusicBox does not imply endorsement by New Music USA.

6 thoughts on “Taking The Plunge

  1. Paul H. Muller

    Congratulations on making the leap to freelance composing – that takes courage and should be admired no matter what the outcome.

    From your article: ” …more often than not I came home from the job frustrated and angry and in no mood to be creative.”

    I also have composed in my spare time while working a full-time job with an hour commute each way. And I often came home with the same frustrations that any job generates. But that frustration motivated me to keep writing and performing – music became my response to the soul-killing nature of corporate life. In my experience art as a counterweight to the emotionally draining demands of the day job is a more powerful stimulus to creativity than waiting for ‘inspiration’.

    As you say, everyone has to find out what works best for them.

    Looking forward to hearing more of your story.

    1. Dennis Tobenski

      Hi Paul,

      Thanks for your comment!

      I absolutely understand using art as a counterbalance to the frustrations of daily life. Some of my most productive periods were when I was angriest at my day job. If something motivates you to write, use it! (And screw waiting for “inspiration”, that fickle mistress, haha!)


  2. Scott

    While I would certainly do my best to hunt down new commissions?

    What are you going to do? Go door-to-door? Seriously, as a composer who thought the performers/commissioners came to the composer not the other way around, how does one hunt down new commissions aside from going to people and asking them to pay me to write a piece of music for them. I don’t have those kinds of balls, I guess.
    More information, please.

    1. Dennis Tobenski

      Hi Scott,

      Quite often, “hunting down new commissions” involves following up on older leads, nudging existing relationships in the right direction, maintaining connections. It’s certainly not, “Excuse me, madam, can I interest you in a set of encyclopedias?”

      In my experience, commissions tend to follow from performances (not all performances, but enough). So “hunting down new commissions” looks more like finding performers who might enjoy the type of music I write, (gently, elegantly) letting them know that my music exists, trying to build relationships with them, hoping that they have a desire/opportunity to perform my music, and just trying to be available for if/when the opportunity arises. At best, it’s a years-long process filled with going to concerts, meeting over drinks, and making new friends who ultimately want to give you money. At worst, it’s years spent going to concerts, meeting over drinks, and making new friends. (Yes, we want commissions, but our relationships aren’t merely transactional.)

      It takes a certain type of balls, absolutely. Balls that I’m still, to this day, growing. But balls that consist of being both assertive and vulnerable. Where you’re prepared to have The Conversation About Money, yet also be empathetic and sensitive and honest and willing-to-wait-until-the-time-is-right.

      When I embarked on this journey, I had some leads on possible commissions. I followed up on them, and some bore fruit. Four years later, most haven’t yet. Some of those will, some won’t. I’m still hunting wabbits. It just may be that it’s duck season.


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